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Abstract:

It has been necessary to use a relatively large amount of cyclodextrin in
order to produce a composite material, but the amount of the cyclodextrin
needs to be reduced from the viewpoint of costs; in this respect, the
present invention provides a composite material comprising a food or
active pharmaceutical ingredient, a phytosterol ester, a medium-chain
fatty acid triacylglyceride, and a cyclodextrin.

Claims:

1. A composite material comprising a food or active pharmaceutical
ingredient, a phytosterol ester, a medium-chain fatty acid
triacylglyceride, and a cyclodextrin.

2. The composite material according to claim 1, which is obtained by
mixing the food or active pharmaceutical ingredient, the phytosterol
ester, the medium-chain fatty acid triacylglyceride, and the cyclodextrin
with each other in the presence of water.

3. The composite material according to claim 1, wherein the food or
active pharmaceutical ingredient is a lipophilic component.

4. The composite material according to claim 3, wherein the lipophilic
component is a pungent component or a bitter component.

5. The composite material according to claim 1, wherein the food or
active pharmaceutical ingredient is a hydrophilic component
surface-treated with a surfactant.

6. A composition comprising the composite material according to claim 1.

7. A liquid composition comprising: the composite material according to
claim 1; water; and a thickener, wherein the composite material is in a
water-dispersed form.

8. A method for producing a composite material comprising a food or
active pharmaceutical ingredient, a phytosterol ester, a medium-chain
fatty acid triacylglyceride, and a cyclodextrin, the method comprising
mixing the food or active pharmaceutical ingredient, the phytosterol
ester, the medium-chain fatty acid triacylglyceride, and the cyclodextrin
with each other in the presence of water, to form the composite material.

9. The method for producing a composite material according to claim 8,
further comprising: dissolving the food or active pharmaceutical
ingredient in the phytosterol ester and the medium-chain fatty acid
triacylglyceride; preparing a mixture containing the cyclodextrin and the
water; and mixing the phytosterol ester and the medium-chain fatty acid
triacylglyceride, in which the food or active pharmaceutical ingredient
is dissolved, with the said mixture, to form the composite material.

Description:

BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention

[0002] The present invention relates to a composite material comprising a
food or active pharmaceutical ingredient, and to a method for producing
the composite material.

[0003] 2. Description of the Related Art

[0004] Capsaicins, which are pungent components of capsicum pepper, are
one example of the lipophilic components having an irritating taste or
odor. Capsaicins are known to have various actions useful for organisms,
such as an action of appetite stimulation, actions of vasodilation and
vasoconstriction, an action of increasing salivation, an action of
increasing gastric acid secretion, an action of increasing peristaltic
movement of the intestinal tract, an action of decreasing the cholesterol
level in the circulatory system, an action of increasing energy
metabolism, and an action of increasing the release of bioactive
peptides. However, capsaicins have a strong pungency, and hence the
application range thereof to foods and beverages has been limited.

[0005] To inhibit the pungency of capsaicins, novel capsaicinoid
glycosides have been proposed which are obtained by modifying the
molecular structure of capsaicinoids to eliminate their strong pungency
(Patent Document 1). However, the capsaicinoid glycosides are novel
chemically synthesized compounds, and hence are not approved yet for use
in foods or beverages.

[0006] Moreover, a masking agent which is characterized by including a
polyglycerin condensed ricinoleate and a food including the masking agent
have been proposed (Patent Document 2). Specifically, a masking
agent-containing chili oil has been disclosed which is obtained by adding
0.1% of a capsicum pepper extract oil and 0.5% of hexaglycerin condensed
ricinoleate to sesame oil. However, the application range of this masking
agent is limited to foods and beverages containing a large amount of an
oil component. In addition, this masking agent is likely to affect the
flavor of foods and beverages because of a waxy odor thereof.

[0007] Furthermore, an edible microcapsule has been proposed which is
characterized in that an edible fat and fatty oil containing capsaicin is
used as a core material, a wall membrane is formed of a protein and a
coacervate agent, and a transglutaminase is used as an agent for curing
and crosslinking the wall membrane (Patent Document 3). However, the
present inventors actually prepared this edible microcapsule and stirred
this edible microcapsule with hot water (at 97° C.) in a beaker.
As a result, the core material leaked, and floating oil was observed.
Therefore, the edible microcapsule was found not to be suitable for
beverages.

[0008] In addition to capsicum pepper, for example, turmeric has been
conventionally used as a spice, a yellow pigment, and a crude drug.
Recently, turmeric has attracted attention as a health food material.
Turmeric has been commercially available as processed foods, processed
beverages, tablets, and the like. A soft capsule preparation is proposed
which is capable of masking the characteristic bitter taste of turmeric
and of effectively preventing change of turmeric with time (Patent
Document 4). The soft capsule preparation is characterized by comprising
a capsule base member mainly containing gelatin, and a target content
with which the capsule base member is filled, wherein the gelatin is
prepared by being dissolved in electrolyzed-reduced water with a pH of 8
to 10 and with a redox potential of -100 mV to -200 mV.

[0009] As described above, the excellent and effective actions of
naturally occurring materials typified by capsicum pepper and turmeric
have attracted attention in the fields of foods and pharmaceuticals. With
increase in demands for natural products and enhancement of health
consciousness, people who want to be healthy favor natural and mild
actions of not only traditional Chinese herbal medicines and crude drugs
but also various materials, such as spices and herbs. Accordingly, these
materials have been increasingly used as raw materials for health foods
and pharmaceuticals.

[0010] Under such circumstances, the present applicant has filed a patent
application for a composite material comprising: a lipophilic component
having an irritating taste and/or odor; a phytosterol ester; and a
cyclodextrin, as a material capable of effectively inhibiting an
irritating taste and/or odor of a lipophilic component having an
irritating taste and/or odor, which is typified by pungent components of
capsaicins, and bitter components of a turmeric extract, and also for a
method for producing the composite material (Patent Document 5).

[0011] In addition, the present applicant also has filed a patent
application for a method for preventing decomposition/deterioration of a
lipophilic component in the presence of water (PCT/JP2009/71473). This
method comprises: forming a composite material containing a lipophilic
component, a phytosterol ester, and a cyclodextrin; and storing the
lipophilic component in the form of the composite material in the
presence of water.

[0012] Moreover, the present applicant has filed a patent application for
a composite material comprising a phytosterol ester, a hydrophilic
component surface-treated with a surfactant, and a cyclodextrin, in order
to provide a material which comprises a hydrophilic component having an
irritating taste or odor such as a bitter or pungent taste, and which is
capable of effectively inhibiting the irritating taste or odor of the
hydrophilic component, and to provide a method for producing the
material, as well as in order to provide a material which comprises a
hydrophilic component decomposable in the presence of water, and which is
capable of effectively preventing the decomposition of the hydrophilic
component with the elapse of time, and to provide a method for producing
the material (Japanese Patent Application No. 2008-328263). [0013] Patent
Document 1: Japanese Patent No. 3156240 [0014] Patent Document 2:
Japanese Patent Application Publication No. 2002-65177 [0015] Patent
Document 3: Japanese Patent Application Publication No. 2003-47432 [0016]
Patent Document 4: Japanese Patent No. 4469660 [0017] Patent Document 5:
International Publication No. WO2009/005005

SUMMARY OF THE INVENTION

[0018] When the composite material is manufactured and used as a business,
the present applicant has encountered a problem of the high costs of raw
materials, particularly of the cyclodextrin. To solve this problem, it is
necessary to reduce the amount of the cyclodextrin, while a desired
effect is obtained.

[0019] The present invention provides a composite material comprising a
food or active pharmaceutical ingredient; a phytosterol ester; a
medium-chain fatty acid triacylglyceride; and a cyclodextrin.

[0020] The present invention also provides a composition comprising the
composite material.

[0021] Moreover, the present invention provides a liquid composition
comprising: the composite material; water; and a thickener, wherein the
composite material is in a water-dispersed form.

[0022] Further, the present invention provides a method for producing a
composite material comprising a food or active pharmaceutical ingredient,
a phytosterol ester, a medium-chain fatty acid triacylglyceride, and a
cyclodextrin, the method comprising: dissolving the food or active
pharmaceutical ingredient in the phytosterol ester and the medium-chain
fatty acid triacylglyceride; preparing a mixture containing the
cyclodextrin and water; and mixing the phytosterol ester and the
medium-chain fatty acid triacylglyceride, in which the food or active
pharmaceutical ingredient is dissolved, with the mixture, to form the
composite material.

EFFECTS OF THE INVENTION

[0023] The present invention makes it possible to provide a composite
material comprising: a food or active pharmaceutical ingredient; a
phytosterol ester; a medium-chain fatty acid triacylglyceride, and a
cyclodextrin, with the amount of the cyclodextrin being reduced.

[0026]FIG. 3 is a graph showing change in ratio of remaining capsinoids
in Reference Example 3 and Reference Comparative Examples 3-1 and 3-2.

[0027]FIG. 4 is a graph showing change of gingerol during storage in
Reference Example 4 and Reference Comparative Example 4.

[0028]FIG. 5 is a graph showing change of shogaol during storage in
Reference Example 4 and Reference Comparative Example 4.

[0029]FIG. 6 is a graph showing change of piperine during storage in
Reference Example 5 and Reference Comparative Example 5.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0030] A composite material of the present invention comprises: a food or
active pharmaceutical ingredient; a phytosterol ester; a medium-chain
fatty acid triacylglyceride; and a cyclodextrin.

[0031] The food or active pharmaceutical ingredient contained in the
composite material of the present invention is not particularly limited,
and the present invention is particularly effective when directed to a
raw material having an irritating taste and/or odor, or a raw material
which easily degrades during storage and is unstable. The composite
material of the present invention presumably has a structure in which the
food or active pharmaceutical ingredient is incorporated into a lipid
comprising the phytosterol ester and the medium-chain fatty acid
triacylglyceride, and is shut off from the outside, i.e., has a kind of a
capsule structure. Accordingly, the food or active pharmaceutical
ingredient employed in the composite material of the present invention is
not particularly limited, as long as the food or active pharmaceutical
ingredient can be incorporated into the lipid comprising the phytosterol
ester and the medium-chain fatty acid triacylglyceride.

[0032] Accordingly, when the food or active pharmaceutical ingredient is a
lipophilic component, the food or active pharmaceutical ingredient has a
high affinity for the phytosterol ester and the medium-chain fatty acid
triacylglyceride. Hence, in such a case, the composite material can be
formed by mixing the food or active pharmaceutical ingredient directly
with the phytosterol ester, the medium-chain fatty acid triacylglyceride,
and the cyclodextrin. Examples of the lipophilic component include
capsaicins, which fall into a class of the lipophilic pungent components.
The capsaicins include capsaicin, dihydrocapsaicin, nordihydrocapsaicin,
homocapsaicin, vanillylnonanamide, and vanillyl butyl ether. Capsicum
pepper extracts such as capsicum oleoresins can be suitably used as a raw
material containing capsaicins, because the extracts contain a large
amount of capsaicins.

[0033] Meanwhile, examples of the lipophilic component other than the
capsaicins include (6)-gingerol, (6)-shogaol, zingerone, and
(8),(10)-shogaol, which are pungent components of ginger; piperine and
piperanine, which are pungent components of pepper; sanshool, which is a
pungent component of Japanese pepper; and the like. A pepper extract, a
ginger extract, and a Japanese pepper extract can be suitably used as raw
materials containing pungent components of ginger, pepper, and Japanese
pepper, respectively.

[0034] In addition to the pungent components, the present invention can be
applied to lipophilic bitter components such as a turmeric extract
containing a lipophilic component having a bitter taste. Moreover, the
present invention can be applied not only to the above-described
lipophilic components of spices, but also to unsaturated fatty acids such
as docosahexaenoic acid and eicosapentaenoic acid.

[0035] In addition, the composite material of the present invention is
found to be capable of preventing the decomposition of the lipophilic
component due to, for example, interaction with water, or interaction
with light, an enzyme, oxygen, heat, or the like in the presence of
water. In other words, the composite material of the present invention
stabilizes the lipophilic component, and improves the storability
thereof. Accordingly, for example, substances having a structure
analogous to those of capsaicins but having no pungency, such as
capsinoids, unsaturated fatty acids, curcumin, which is a pigment
component of turmeric, and the like can be suitably used as the
lipophilic component. The composite material of the present invention is
effective for improvement in stability of these substances.

[0036] When the food or active pharmaceutical ingredient is a hydrophilic
component, the food or active pharmaceutical ingredient is preferably a
hydrophilic component surface-treated with a surfactant in order to
increase the affinity for the phytosterol ester and the medium-chain
fatty acid triacylglyceride. Examples of the hydrophilic components
include caffeine, B vitamins, betanin, isobetanin, and the like.

[0037] Caffeine is a component contained in coffee, black tea, and the
like. Caffeine has a strong bitter taste, and is known to have
physiological effects such as sleepiness prevention, stress relaxation,
and obesity prevention.

[0038] B vitamins collectively refer to eight kinds of water-soluble
vitamins, including vitamin B1, vitamin B2, niacin, pantothenic acid,
vitamin B6, vitamin B12, folic acid, and biotin, and are also referred to
as a vitamin B complex. B vitamins are often contained in beans or seeds
such as soybean, pork or beef liver, and the like. B vitamins are used in
organisms as raw materials of coenzymes, and hence are necessary for
metabolism in the body.

[0039] Betanin and isobetanin are main components of the red pigment
contained in red beet, and used as a natural edible pigment. The pigment
has a vivid red color, and undergoes less change in color due to pH. The
pigment is known to be stable in the pH range of 4 to 7, but is unstable
to heat.

[0040] The phytosterol ester used in the present invention is a substance
obtained by ester-bonding a fatty acid to a hydroxyl group in the sterol
skeleton of a phytosterol. Examples of a method for producing the
phytosterol ester include an enzymatic method utilizing an enzyme, and
the like. Examples of the enzymatic method include a method of obtaining
the phytosterol ester by mixing a phytosterol and a fatty acid and
causing a reaction therebetween (at 30 to 50° C. for approximately
48 hours) with a lipase or the like used as a catalyst; and the like.
Examples of other synthesis methods include a method of obtaining a
phytosterol ester by esterification of a phytosterol produced from
soybean or the like with a fatty acid obtained from rapeseed oil, corn
oil, or her like, by dehydration in the presence of a catalyst; and the
like.

[0041] Examples of the phytosterol include sterols contained in vegetable
fats and fatty oils, and the like. For example, the phytosterol may be
one extracted and purified from a vegetable fat or fatty oil of soybean,
rapeseed, cottonseed, or the like. The phytosterol may be a mixture
containing β-sitosterol, campesterol, stigmasterol, brassicasterol,
fucosterol, dimethylsterol, and the like. For example, a soybean sterol
contains 53 to 56% of sitosterol, 20 to 23% of campesterol, and 17 to 21%
of stigmasterol. A phytosterol which is commercially available as
"Phytosterol F" (produced by TAMA BIOCHEMICAL CO., LTD.) can also be used
as the phytosterol.

[0043] Preferred examples of the phytosterol ester include phytosterol
esters each obtained from a phytosterol derived from soybean and a fatty
acid derived from rapeseed oil; phytosterol esters each obtained from a
phytosterol derived from soybean or rapeseed and a fatty acid derived
from palm oil; and the like. The former include "San Sterol NO. 3" of
San-Ei Gen F. F. I., Inc., and the like. The latter include "Phytosterol
Fatty Acid Ester" of TAMA BIOCHEMICAL CO., LTD., and the like.

[0044] The medium-chain fatty acid triacylglyceride used in the present
invention is a triglyceride whose constituent is a medium-chain fatty
acid, namely octanoic acid (trivial name: caprylic acid), which is a
fatty acid having 8 carbon atoms, or decanoic acid (trivial name: capric
acid), which is a fatty acid having 10 carbon atoms.

[0045] The cyclodextrin used in the present invention is a cyclic
non-reducing maltooligosaccharide, whose constitutional unit is glucose.
Any of α-cyclodextrin with six glucose units, β-cyclodextrin
with seven glucose units, and γ-cyclodextrin with eight glucose
units can be used as the cyclodextrin. γ-Cyclodextrin is preferable
from the viewpoint that γ-cyclodextrin is decomposed by human
digestive enzymes, and has high solubility in water, and accordingly
γ-cyclodextrin is used for foods and beverages, particularly for
beverages, without reluctance.

[0046] The composite material of the present invention is obtainable by
mixing the food or active pharmaceutical ingredient, the phytosterol
ester, the medium-chain fatty acid triacylglyceride, and the cyclodextrin
with each other in the presence of water. For producing the composite
material of the present invention, the amounts of the phytosterol ester
and the medium-chain fatty acid triacylglyceride are, for example,
preferably such that the total amount of the phytosterol ester and the
medium-chain fatty acid triacylglyceride is 0.5 to 30000 parts by weight
with respect to 1 part by weight of the food or active pharmaceutical
ingredient, although the amounts vary depending on the target food or
active pharmaceutical ingredient. Meanwhile, the amount of the
cyclodextrin is, for example, preferably 0.00135 to 135 parts by weight
with respect to 1 part by weight of the total amount of the phytosterol
ester and the medium-chain fatty acid triacylglyceride. When a
homogenizing process is conducted with a homogenizer, the amount of the
cyclodextrin is more preferably 0.00135 to 15 parts by weight with
respect to 1 part by weight of the total amount of the phytosterol ester
and the medium-chain fatty acid triacylglyceride. In addition, the amount
of water coexistent during the production of the composite material is,
for example, preferably 0.01 to 100 parts by weight, and more preferably
0.1 to 10 parts by weight, with respect to 1 part by weight of the
cyclodextrin. In addition, when the surface of the hydrophilic component
is treated with a surfactant, the amount of the surfactant is, for
example, preferably 0.0001 to 10 parts by weight, and more preferably
0.0001 to 10 parts by weight, with respect to 1 part by weight of the
hydrophilic component. In addition, when the composite material of the
present invention is produced, the mixing is preferably conducted under
heating at 40 to 90° C., and more preferably 50 to 85° C.

[0047] In addition, in the composite material of the present invention,
the ratio between the phytosterol ester and the medium-chain fatty acid
triacylglyceride is 9:1 to 1:9, and more preferably 7:3 to 3:7 in terms
of weight ratio.

[0048] More specifically, the composite material of the present invention
can be produced by any one of the following methods (1) to (3); however,
the method (1) is particularly preferable in order to more effectively
inhibit the taste or odor of the food or active pharmaceutical
ingredient:

[0049] (1) a method comprising dissolving the food or active
pharmaceutical ingredient in a phytosterol ester and the medium-chain
fatty acid triacylglyceride, preparing a mixture containing the
cyclodextrin and water, and mixing the phytosterol ester and the
medium-chain fatty acid triacylglyceride, in which the food or active
pharmaceutical ingredient is dissolved, with the mixture;

[0050] (2) a method comprising preparing a mixture containing the
cyclodextrin, water, the phytosterol ester, and the medium-chain fatty
acid triacylglyceride, and mixing the food or active pharmaceutical
ingredient and water with the mixture; and

[0051] (3) a method comprising preparing a mixture containing the food or
active pharmaceutical ingredient and the cyclodextrin, and mixing water,
the phytosterol ester, and the medium-chain fatty acid triacylglyceride
with the mixture.

[0052] Of these methods, the method (1) is more specifically described
below. Specifically, when the food or active pharmaceutical ingredient
is, for example, capsaicins, 1 part by weight of the capsaicins are
dissolved in 30 to 30000 parts by weight, in total, of the phytosterol
ester and the medium-chain fatty acid triacylglyceride in the step of
dissolving the food or active pharmaceutical ingredient in the
phytosterol ester and the medium-chain fatty acid triacylglyceride,
although this ratio varies depending on the target food or active
pharmaceutical ingredient. For dissolving the food or active
pharmaceutical ingredient in the phytosterol ester, the food or active
pharmaceutical ingredient is preferably dissolved in such a way that the
food or active pharmaceutical ingredient is added to the phytosterol
ester and the medium-chain fatty acid triacylglyceride, and the resultant
mixture is warmed to 40 to 80° C., preferably 50 to 70° C.
Alternatively, the food or active pharmaceutical ingredient may be
dissolved in such a way that the phytosterol ester and the medium-chain
fatty acid triacylglyceride are warmed to 40 to 80° C., preferably
50 to 70° C. in advance, and then the food or active
pharmaceutical ingredient is added thereto.

[0053] In the step of preparing the mixture containing the cyclodextrin
and water, the amounts of the cyclodextrin and water are not particularly
limited, as long as the composite material can be formed later with these
amounts. For example, the amount of the cyclodextrin is, for example,
0.00135 to 135 parts by weight with respect to 1 part by weight of the
total amount of the phytosterol ester and the medium-chain fatty acid
triacylglyceride. When a homogenizing process is conducted with a
homogenizer, the amount of the cyclodextrin is preferably 0.00135 to 15
parts by weight with respect to 1 part by weight of the total amount of
the phytosterol ester and the medium-chain fatty acid triacylglyceride.
Meanwhile, the amount of water is, for example, 0.01 to 100 parts by
weight, and preferably 0.1 to 10 parts by weight, with respect to 1 part
by weight of the cyclodextrin.

[0054] In the step of mixing the phytosterol ester, in which the food or
active pharmaceutical ingredient is dissolved, with the mixture, the
mixing is continued until the composite material of the present invention
is formed. The thus formed composite material is deposited as particulate
matters in the lower part of water, after the mixing is stopped and the
mixture is allowed to stand for a while. Note that the mixing here is
performed preferably by using a mixing apparatus with high shearing
force, such as a kneader, for forming the composite material by
thoroughly kneading these components.

[0055] The obtained composite material can be in any form. For example,
the composite material may be formed into a powder form or a granular
form by using an excipient or the like. In addition, the composite
material may be in a liquid form or a paste form, where the composite
material is dispersed or emulsified in a solvent such as water.

[0056] The thus obtained composite material of the present invention is
advantageous in that the irritating taste and/or odor of the lipophilic
component is effectively inhibited. The inhibition of the irritating
taste and/or odor of the composite material of the present invention has
a mechanism different form that of what is called as masking involving
addition of, for example, a sweet component or the like. It is uncertain
what structure the composite material of the present invention has.
However, the lipophilic component contained in the composite material of
the present invention is presumably at least in such a state that the
lipophilic component cannot bind to the receptor of the taste.

[0057] In addition, the composite material of the present invention is
advantageous in that no separation of an oil component occurs.
Incidentally, when a composite material is produced by using a different
oil instead of the phytosterol ester, a homogeneous composite material
cannot be obtained, and separation of an oil component occurs. Hence,
when blended into a beverage or the like, the composite material has a
problem that the oil component floats and attaches to the inner surface
of a container. In contrast, the composite material of the present
invention is advantageous in that the use of the phytosterol ester makes
it possible to obtain a homogeneous composite material, and that an oil
component does not separate, and hence no oil component attaches onto the
inner surface of a container, when the composite material is blended into
a beverage or the like.

[0058] Moreover, the composite material of the present invention is also
thermally stable. For example, even when the composite material is
blended into a food or beverage, and heated to 65 to 100° C., the
irritating taste and/or odor of the lipophilic component can be
inhibited, and no separation of an oil component occurs.

[0059] The composite material of the present invention is easily dispersed
in water. Hence, the composite material can be blended into foods,
beverages, pharmaceutical drugs, cosmetics, and the like, and provided as
various compositions. More specifically, examples of foods and beverages
into which the composite material of the present invention is blended
include beverages, jellies, tablets, and the like. Here, a case where the
composite material of the present invention is blended into a beverage is
taken as an example. A heat-sterilized packed beverage can be produced,
for example, as follows. Specifically, the composite material of the
present invention is added to water. An acidulant is added thereto to
adjust the pH to 4.0 or less, and preferably 2.5 to 3.5. Raw materials
such as a sweetener, a fruit juice, a flavor, a coloring matter, and
vitamin C are added thereto, and mixed. This mixture is heated to 65 to
100° C. for sterilization treatment, and then packed and sealed in
a container. Moreover, a packed jelly can be produced by adding a
gelatinizing agent to the raw materials.

[0060] The composition of the present invention can also be provided as a
liquid composition which comprises the composite material, water, and a
thickener, and which is in a form where the composite material is
dispersed in water. Specifically, although the composite material tends
to be deposited in water, the inclusion of the thickener makes it
possible to provide a liquid composition in which the composite material
is dispersedly held in water. In addition, this liquid composition can
also be provided as a packed liquid composition such as a packed
beverage. In this case, there are advantages in that no separation of an
oil component occurs in the container, and hence no oil component
attaches onto the inner surface of the container.

[0062] The amount of the thickener is not particularly limited, as long as
the composite material can be dispersed in water with the amount. For
example, the liquid composition preferably contains 0.01 to 1.0% by
weight of the thickener.

[0064] Separately, 1.1 parts by weight of γ-cyclodextrin was
dissolved in 1.097 parts by weight of water (80° C.).

[0065] To the γ-cyclodextrin solution, the solution of the capsicum
oleoresin, the medium-chain fatty acid triacylglyceride, and the
phytosterol ester was added. After a preliminary homogenization treatment
(at 5000 rpm for 10 minutes), a high-pressure homogenization treatment
(at 100 MPa, a three-plunger type) was further conducted. Thus, a
composite material was obtained.

(2) Production of Beverage

[0066] Citric acid, trisodium citrate, xanthan gum, sucralose, and water
were added to the composite material, and the substances were mixed with
each other with stirring. Subsequently, the mixture was heated to
93° C. with string, and heat sterilized by being held for 3
minutes. After that, the mixture was packed into a container, and cooled.
Thus, a packed beverage was produced. The thus obtained beverage had a
weaker pungency than the beverage obtained in the following Comparative
Example 1. Note that the blending ratio of the beverage is as shown in
the following Table 1.

Comparative Example 1

(1) Production of Composite Material

[0067] With string, 0.00284 parts by weight of a capsicum oleoresin
(content of capsaicins: 35.21% by weight) and 0.3000 parts by weight of a
phytosterol ester ("San Sterol No. 3" manufactured by San-Ei Gen F. F.
I., Inc.) were heated to 80° C.

[0068] Separately, 1.1 parts by weight of γ-cyclodextrin was
dissolved in 1.097 parts by weight of water (80° C.).

[0069] To the γ-cyclodextrin solution, the solution of the capsicum
oleoresin and the phytosterol ester was added. After a preliminary
homogenization treatment (at 5000 rpm for 10 minutes), a high-pressure
homogenization treatment (at 100 MPa, a three-plunger type) was further
conducted. Thus, a composite material was obtained.

(2) Production of Beverage

[0070] Citric acid, trisodium citrate, xanthan gum, sucralose, and water
were added to the composite material, and the substances were mixed with
each other with stirring. Subsequently, the mixture was heated to
93° C. with string, and heat sterilized by being held for 3
minutes. After that, the mixture was packed into a container, and cooled.
Thus, a packed beverage was produced. A strong pungency was noticed from
the thus obtained beverage. Note that the blending ratio of the beverage
is as shown in the following Table 1.

[0071] Composite materials and beverages were produced in the same manner
as in Example 1, except that the ratio between the phytosterol ester and
the medium-chain fatty acid triacylglyceride was changed to the ratios
shown in Table 2. Table 2 shows sensory evaluation results of the
beverages.

Comparative Example 2

[0072] With string, 0.00284 parts by weight of a capsicum oleoresin
(content of capsaicins: 35.21% by weight) and 0.3000 parts by weight of a
medium-chain fatty acid triacylglyceride ("MCT-1" manufactured by J-OIL
MILLS, Inc.) were heated to 80° C.

[0073] Separately, 1.1 parts by weight of γ-cyclodextrin was
dissolved in 1.097 parts by weight of water (80° C.).

[0074] To the γ-cyclodextrin solution, the solution of the capsicum
oleoresin and the phytosterol ester was added. A preliminary
homogenization treatment (at 5000 rpm for 10 minutes) was conducted.
However, the fluidity was lost at this point, and the high-pressure
homogenizer was unable to be conducted.

[0075] Note that approximately 8150 parts by weight of
γ-cyclodextrin was used, in Example 1 of Patent Document 5, with
respect to 1 part by weight of capsaicins to obtain a beverage from which
almost no pungency was noticed. In contrast, it was found that, in
Example 2 and Example 3 of the present invention, the use of only
approximately 1100 parts by weight (approximately 1/7.4) of
γ-cyclodextrin with respect to 1 part by weight of capsaicins
astonishingly made it possible to obtain beverages from which almost no
pungency was noticed, as in the case with Example 1 of Patent Document 5.

Example 4

(1) Production of Composite Material

[0076] To 0.06 parts by weight of a phytosterol ester ("San Sterol No. 3"
manufactured by San-Ei Gen F. F. I., Inc.) and 0.04 parts by weight of a
medium-chain fatty acid triglyceride ("MCT-1" manufactured by J-OIL
MILLS, Inc.), which were heated to 80° C., 0.015 parts by weight
of a ginger extract (shogaol: 10%) was added, and dissolved therein.

[0077] Separately, 0.37 parts by weight of γ-cyclodextrin and 0.37
parts by weight of water were mixed with each other by using a TK
homomixer, while being heated to 80° C.

[0078] To the γ-cyclodextrin solution, 0.115 parts by weight of the
oil phase in which the ginger extract was dissolved was added. While
continuously being heated to 80° C., the mixture was stirred with
a TK homomixer to conduct preliminary emulsification.

[0079] After the preliminary emulsification, the mixture was passed
through a high-pressure homogenizer (LAB1000 manufactured by SMT Co.,
Ltd., pressure: 100 MPa). Thus, a ginger extract-containing composite
material was prepared.

(2) Production of Beverage

[0080] Into 97.705 parts by weight of water, 0.855 parts by weight of the
composite material, 0.3 parts by weight of citric acid, 0.12 parts by
weight of trisodium citrate, 0.72 parts by weight of
γ-cyclodextrin, and 0.3 parts by weight of a phytosterol
preparation (manufactured by San-Ei Gen) were dispersed, and the
dispersion was stirred with a mixer for 30 seconds. Thus, a model
beverage containing the ginger extract composite material was prepared.
The model beverage was heated up to 93° C., sterilized by being
held at 90° C. for 3 minutes, and then packed into a pouch.
Thereafter, the pouch was held in a constant-temperature water bath at
83° C. for 5 minutes to perform a second sterilization.

Comparative Example 3

(1) Production of Composite Material

[0081] To 0.06 parts by weight of a phytosterol ester ("San Sterol No. 3"
manufactured by San-Ei Gen F. F. I., Inc.), which was heated to
80° C., 0.015 parts by weight of a ginger extract (shogaol: 10%)
was added, and dissolved therein.

[0082] Separately, 0.37 parts by weight of γ-cyclodextrin and 0.37
parts by weight of water were mixed with each other by using a TK
homomixer, while being heated to 80° C.

[0083] To the γ-cyclodextrin solution, 0.075 parts by weight of the
oil phase in which the ginger extract was dissolved was added. While
continuously being heated to 80° C., the mixture was stirred with
a TK homomixer to conduct preliminary emulsification.

[0084] After the preliminary emulsification, the mixture was passed
through a high-pressure homogenizer (LAB1000 manufactured by SMT Co.,
Ltd., pressure: 100 MPa). Thus, a ginger extract-containing composite
material was prepared.

(2) Production of Beverage

[0085] Into 97.745 parts by weight of water, 0.815 parts by weight of the
composite material, 0.3 parts by weight of citric acid, 0.12 parts by
weight of trisodium citrate, 0.72 parts by weight of
γ-cyclodextrin, and 0.3 parts by weight of a phytosterol
preparation (manufactured by San-Ei Gen) were dispersed, and the
dispersion was stirred with a mixer for 30 seconds. Thus, a model
beverage containing a ginger extract composite material was prepared. The
model beverage was heated up to 93° C., sterilized by being held
at 90° C. for 3 minutes, and then packed into a pouch. Thereafter,
the pouch was held in a constant-temperature water bath at 83° C.
for 5 minutes to conduct a second sterilization.

[0086] The model beverages prepared in Example 4 and Comparative Example 3
were stored at 60° C. The amount of shogaol in each sample before
the storage and after two-week storage was quantitatively determined by
liquid chromatography. As the ratio of remaining shogaol, a value of each
sample determined after the two-week storage was represented by
percentage, with a value of each sample before the storage (0 weeks)
being employed as 100%. Table 4 shows the results.

Pretreatment Method for Liquid Chromatography

[0087] Each model beverage (25 g) was centrifuged (at 3000 rpm for 10
minutes), and then the supernatant was removed. To the deposit, 3 ml of
DMSO (dimethyl sulfoxide) was added, and the mixture was ultrasonicated
to dissolve the deposit. Moreover, the mixture was diluted with methanol
to 50 ml, filtered through a 0.45-μm filter, and then used as a test
liquid.

[0089] As is apparent from Table 4, the decomposition of shogaol was more
prevented in Example 4 than in Comparative Example 3. In other words, it
has been found that the addition of the medium-chain fatty acid
triglyceride enables further improvement of the stability of the active
ingredients in the ginger extract.

[0090] Hereinafter, Examples of PCT/JP2009/71473 are described as
Reference Examples of the food or active pharmaceutical ingredient
(lipophilic component) to which the present invention can be applied.

Reference Example 1

[0091] To 5.67 parts by weight of a phytosterol ester melted by heating to
60° C., 0.63 parts by weight of a mustard essential oil was added,
and dissolved therein. Meanwhile, 62.4 parts by weight of
γ-cyclodextrin and 31.3 parts by weight of water (75° C.)
were added to a mortar, and mixed with each other by using a pestle to
obtain a paste. To this paste, the above-described phytosterol ester in
which the mustard essential oil was dissolved was added, and the mixture
was kneaded in a hot water (75° C.) for 10 minutes. After
completion of the kneading, water in an amount equivalent to water lost
due to vaporization was added thereto, and the mixture was kneaded again
to homogeneity. The blended amounts (g) in Reference Example 1 are shown
in the following Table 5.

Reference Comparative Example 1

[0092] Into a mortar, 66.24 parts by weight of γ-cyclodextrin and
33.13 parts by weight of water (60° C.) were added, and mixed with
each other by using a pestle to obtain a paste. To this paste, 0.63 parts
by weight of a mustard essential oil was added, and the mixture was
kneaded in hot water (75° C.) for 10 minutes. After completion of
the kneading, water in an amount equivalent to water lost due to
vaporization was added thereto, and the mixture was kneaded again to
homogeneity. The blended amounts (g) in Reference Comparative Example 1
are shown in the following Table 5.

[0093] To 1 part by weight of each of the samples obtained in Reference
Example 1 and Reference Comparative Example 1, 5 parts by weight of water
was added, and the sample was uniformly dispersed therein. GC vials were
filled up with the samples of the composite materials dispersed in water,
and then each GC vial was tightly closed with a cap, and sealed in an
aluminum pouch. These vials were stored at 50° C.

(GC Measurement)

[0094] The samples stored for 0 days (at the beginning of the storage), 1
day, and 6 days were diluted 100-fold with hexane, allowed to stand at
room temperature for 16 to 18 hours, and filtered through a 0.45-μm
filter to prepare GC samples. For the GC measurement, a FID detector was
used. The GC measurement was carried out under the following conditions.

[0096]FIG. 1 shows change in allyl concentration. As shown in FIG. 1, the
decomposition of allyl isothiocyanate in the oil was apparently prevented
by storing the mustard essential oil in the presence of water in the form
of the composite material which was formed together with the phytosterol
ester and the γ-cyclodextrin. Note that the ratio of allyl
isothiocyanate remaining after 6-day storage was 60.2% in Reference
Example 1 and 15.5% in Reference Comparative Example 1, relative to that
at the beginning of the storage.

Reference Example 2

[0097] To 3.5 parts by weight of a phytosterol ester melted by heating to
60° C., 0.07 parts by weight of a capsicum oleoresin was added,
and dissolved therein. Into a mortar, 64.3 parts by weight of
γ-cyclodextrin and 32.13 parts by weight of water (60° C.)
were added, and mixed with each other by using a pestle to obtain a
paste. To this paste, the above-described phytosterol ester in which the
capsicum oleoresin was dissolved was added, and the mixture was kneaded
in hot water (60° C.) for 10 minutes. After completion of the
kneading, water in an amount equivalent to water lost due to vaporization
was added thereto, and the mixture was kneaded again to homogeneity. The
blended amounts (g) in Reference Example 2 are shown in the following
Table 6.

Reference Comparative Example 2

[0098] Into a mortar, 66.6 parts by weight of γ-cyclodextrin and
33.33 parts by weight of water (60° C.) were added, and mixed with
each other by using a pestle to obtain a paste. To this paste, 0.07 parts
by weight of a capsicum oleoresin was added, and the mixture was kneaded
in hot water (60° C.) for 10 minutes. After completion of the
kneading, water in an amount equivalent to water lost due to vaporization
was added thereto, and the mixture was kneaded again to homogeneity. The
blended amounts (g) in Reference Comparative Example 2 are shown in the
following Table 6.

[0099] Each of the samples obtained in Reference Example 2 and Reference
Comparative Example 2 was diluted 10-fold with a 50 mM tris buffer
(capsaicin concentration: 0.0028%). To this liquid, an acylase was added
at a concentration of 0.05 u/ml. The mixture was shaken in a
constant-temperature water bath at 37° C. to allow the reaction of
the enzyme to proceed.

[0100] Meanwhile, as Reference Example, a capsaicin reagent (capsaicin
content: 95% or more) manufactured by SIGMA was diluted with a 50 mM tris
buffer such that the capsaicin concentration was the same as that
(0.0028%) in Reference Example 2 and Reference Comparative Example 2. To
this liquid, an acylase was added at a concentration of 0.05 u/ml. The
mixture was shaken in a constant-temperature water bath at 37° C.
in the same manner as in Reference Example 2 and Reference Comparative
Example 2, to allow the reaction of the enzyme to proceed.

(HPLC Measurement)

[0101] To 2 ml of each sample in which the reaction of the enzyme was
allowed to proceed for 0 (at the beginning of the shaking) minutes, 30
minutes, or 60 minutes, 3 ml of water was added, and thus the volume
thereof was adjusted to 5 ml. Moreover, 1 ml of 2.5 N NaOH was added
thereto, followed by heating in boiling water at 100° C. for 10
minutes. After the heating, 20 ml of methanol was added thereto. To this
mixture, 1 ml of 2.5 N HCl was added, and the mixture was diluted with
methanol to 50 ml. Then, the mixture was filtered though a 0.45-μm
filter, and used as a HPLC sample. For the HPLC measurement, a
fluorescence detector was used. The measurement was carried out under the
following conditions.

[0103]FIG. 2 shows change in capsaicin concentration. As shown in FIG. 2,
the decomposition of capsaicin in the capsicum oleoresin was apparently
prevented by storing the capsicum oleoresin in the presence of water in
the form of the composite material which was formed together with the
phytosterol ester and the γ-cyclodextrin. Note that the ratio of
capsaicin remaining after the enzymatic reaction for 60 minutes was 78.6%
in Reference Example 2, 58.9% in Reference Comparative Example 2, and
2.0% in Reference Example, relative to that at the beginning of the
shaking.

[0105] To 0.70 parts by weight of a phytosterol ester heated to 70°
C., 0.35 parts by weight of a fat and fatty oil containing the capsinoids
was added, and dissolved therein. Meanwhile, 7.0 parts by weight of
γ-cyclodextrin and 3.5 parts by weight of water were added to a
mortar, and mixed with each other in a hot water bath at 70° C. to
obtain a paste. To this paste, 1.05 parts by weight of the
above-described oil phase in which the capsinoids were dissolved were
added, and the mixture was kneaded in a hot water bath at 70° C.
for 10 minutes. Thus, a composite material was prepared. Into 87.6 parts
by weight of water, 11.55 parts by weight of the obtained composite
material, 0.56 parts by weight of citric acid, and 0.27 parts by weight
of trisodium citrate were dispersed, and the dispersion was stirred with
a mixer for 30 seconds. Thus, a model beverage containing the composite
material was prepared. The model beverage containing the composite
material was heated up to 93° C., sterilized by being held at
90° C. for 3 minutes, and then packed into a pouch. Thereafter,
the pouch was held in a constant-temperature water bath at 83° C.
for 7 minutes to perform second sterilization.

[0107] To 0.70 parts by weight of refined rapeseed oil heated to
70° C., 0.35 parts by weight of a fat and fatty oil containing the
capsinoids was added, and dissolved therein. To 10.2 parts by weight of
water, 0.33 parts by weight of an emulsifier (a polyglycerin fatty acid
ester SWA-10D manufactured by Mitsubishi-Kagaku Foods Corporation), and
1.05 parts by weight of the above-described oil phase in which the
capsinoids were dissolved were added, and the mixture was emulsified with
a mixer. Thus, an emulsion was prepared. Into 87.6 parts by weight of
water, 11.58 parts by weight of the obtained emulsion, 0.56 parts by
weight of citric acid, and 0.27 parts by weight of trisodium citrate were
dispersed, and the dispersion was stirred with a mixer for 30 seconds.
Thus, an emulsion-containing model beverage was prepared. The
emulsion-containing model beverage was heated up to 93° C.,
sterilized by being held at 90° C. for 3 minutes, and then packed
into a pouch. Thereafter, the pouch was held in a constant-temperature
water bath at 83° C. for 7 minutes to perform second
sterilization.

[0109] To 0.70 parts by weight of refined rapeseed oil heated to
70° C., 0.35 parts by weight of a fat and fatty oil containing the
capsinoids were added, and dissolved therein. Meanwhile, 7.0 parts by
weight of γ-cyclodextrin and 3.5 parts by weight of water were
added to a mortar, and mixed with each other in a hot water bath at
70° C. to obtain a paste. To this paste, 1.05 parts by weight of
the above-described oil phase in which the capsinoids were dissolved was
added, and the mixture was kneaded in a hot water bath at 70° C.
for 10 minutes. Thus, a composite material was prepared. Into 87.6 parts
by weight of water, 11.55 parts by weight of the obtained composite
material, 0.56 parts by weight of citric acid, 0.27 parts by weight of
trisodium citrate were dispersed, and the dispersion was stirred with a
mixer for 30 seconds. Thus, a model beverage containing the composite
material was prepared. The model beverage containing the composite
material was heated up to 93° C., and sterilized by being held at
90° C. for 3 minutes, and then packed into a pouch. Thereafter,
the pouch was held in a constant-temperature water bath at 83° C.
for 7 minutes to perform second sterilization.

[0110] The model beverages prepared in Reference Example 3 and Reference
Comparative Examples 3-1 and 3-2 were stored at 40° C. After
certain periods of time had elapsed, the capsinoids in the samples were
quantitatively determined by liquid chromatography. As the ratio of
remaining capsinoids, values determined after the beverages were stored
for 1 day, 5 days, and 25 days at 40° C. were represented by
percentage, with a value of the capsinoids immediately after the
beginning of the storage (0 days) being employed as 100%. FIG. 3 shows
the results. As is apparent from FIG. 3, the decomposition of the
capsinoids during the storage at 40° C. was more remarkably
prevented in Reference Example 3 than in Reference Comparative Examples
3-1 and 3-2. From the results described above, it has been found that the
present invention makes it possible to prevent the decomposition of
capsinoids in the presence of water, and improve the stability thereof.

Pretreatment Method for Liquid Chromatography

[0111] Regarding each of Reference Example 3 and Reference Comparative
Example 3-2, 12.5 g of the model beverage was centrifuged (at 3000 rpm
for 10 minutes), and then the supernatant was removed. To the deposit, 6
ml of DMSO (dimethyl sulfoxide) was added, and the mixture was
ultrasonicated to dissolve the deposit. Moreover, the mixture was diluted
with methanol to 25 ml, filtered through a 0.45-μm filter, and then
used as a test liquid.

[0112] Regarding Reference Comparative Example 3-1, 5 g of the model
beverage was sampled. The sample was diluted with methanol to 10 ml,
filtered through a 0.45-μm filter, and then used as a test liquid.

[0115] A supercritical ginger extract (gingerol: 24.8%, shogaol: 10.7%,
Takasago International Corporation) was used as a ginger extract.

[0116] To 0.18 parts by weight of a phytosterol ester and 0.12 parts by
weight of an edible fat and fatty oil, which were heated to 80°
C., 0.015 parts by weight of the ginger extract was added and dissolved
therein. Meanwhile, 1.093 parts by weight of γ-cyclodextrin and
1.093 parts by weight of water were mixed with each other by using a TK
homomixer, while being heated to 80° C. To this mixture, 0.315
parts by weight of the above-described oil phase in which the ginger
extract was dissolved was added. While continuously being heated to
80° C., the resultant mixture was stirred with a TK homomixer to
conduct preliminary emulsification. After the preliminary emulsification,
the mixture was passed through a high-pressure homogenizer (LAB1000
manufactured by SMT Co., Ltd., pressure: 100 MPa). Thus, a ginger
extract-containing composite material was prepared. Into 97.08 parts by
weight of water, 2.5 parts by weight of the obtained composite material,
0.3 parts by weight of citric acid, and 0.12 parts by weight of trisodium
citrate were dispersed, and the dispersion was stirred for 30 seconds
with a mixer. Thus, a model beverage containing the ginger extract
composite material was prepared. The model beverage containing the ginger
extract composite material was heated up to 93° C., sterilized by
being held at 90° C. for 3 minutes, and packed into a pouch.
Thereafter, the pouch was held in a constant-temperature water bath at
83° C. for 5 minutes to perform second sterilization. The gingerol
component was 36.1 ppm, and the shogaol component was 15.4 ppm, in the
prepared model beverage containing the ginger extract composite material.

[0118] Into 99.35 parts by weight of water, 0.23 parts by weight of the
emulsion preparation, 0.3 parts by weight of citric acid, and 0.12 parts
by weight of trisodium citrate were dispersed, and the dispersion was
stirred with a mixer for 30 seconds. Thus, a model beverage containing
the ginger extract emulsion preparation was prepared. The model beverage
containing the ginger extract emulsion preparation was heated up to
93° C., sterilized by being held at 90° C. for 3 minutes,
and then packed into a pouch. Thereafter, the pouch was held in a
constant-temperature water bath at 83° C. for 5 minutes to perform
a second sterilization. The gingerol component was 40.9 ppm, and the
shogaol component was 16.2 ppm, in the prepared model beverage containing
the ginger extract emulsion preparation.

[0119] The model beverages prepared in Reference Example 4 and Reference
Comparative Example 4 were stored at 60° C. The gingerol and
shogaol in the samples before the storage, after one-week storage, and
after two-week storage were quantitatively determined by liquid
chromatography. As the ratios of remaining gingerol and shogaol, the
values after one-week storage and two-week storage were represented by
percentage, with each of the values before the storage (0 weeks) being
employed as 100%. FIGS. 4 and 5 show the results. As is apparent from
FIGS. 4 and 5, the decomposition of gingerol and especially of shogaol
was more prevented in Reference Example 4 than in Reference Comparative
Example 4. From the results described above, it has been found that the
present invention makes it possible to prevent the decomposition of a
ginger extract in the presence of water, and to improve the stability
thereof.

Pretreatment Method for Liquid Chromatography

[0120] Regarding Reference Example 4, 25 g of the model beverage was
centrifuged (at 3000 rpm, 10 minutes), and then the supernatant was
removed. To the deposit, 3 ml of DMSO (dimethyl sulfoxide) was added, and
the mixture was ultrasonicated to dissolve the deposit. Moreover, the
mixture was diluted with methanol to 50 ml, filtered through a 0.45-μm
filter, and then used as a test liquid.

[0121] Regarding Reference Comparative Example 4, 25 g of the model
beverage was sampled. The sample was diluted with methanol to 50 ml,
filtered through a 0.45-μm filter, and then used as a test liquid.

[0123] A piperine powder (piperine content: 92% or more, Inabata Koryo
Co., Ltd.) was used as a pepper extract.

[0124] To 0.18 parts by weight of a phytosterol ester and 0.12 parts by
weight of an edible fat and fatty oil, which were heated to 80°
C., 0.0064 parts by weight of the pepper extract was added, and dissolved
therein. Meanwhile, 1.097 parts by weight of γ-cyclodextrin and
1.097 parts by weight of water were mixed with each other by using a TK
homomixer, while being heated to 80° C. To this mixture, 0.3064
parts by weight of the above-described oil phase in which the pepper
extract was dissolved was added. While continuously being heated to
80° C., the resultant mixture was stirred with a TK homomixer to
conduct preliminary emulsification. After the preliminary emulsification,
the mixture was passed through a high-pressure homogenizer (LAB1000
manufactured by SMT Co., Ltd., pressure: 100 MPa). Thus, a pepper
extract-containing composite material was prepared. Into 97.08 parts by
weight of water, 2.5 parts by weight of the obtained composite material,
0.3 parts by weight of citric acid, and 0.12 parts by weight of trisodium
citrate were dispersed, and the dispersion was stirred with a mixer for
30 seconds. Thus, a model beverage containing the pepper extract
composite material was prepared. The model beverage containing the pepper
extract composite material was heated to 93° C., and sterilized by
being held at 90° C. for 3 minutes, and then packed into a pouch.
Thereafter, the pouch was held in a constant-temperature water bath at
83° C. for 5 minutes to conduct a second sterilization. The amount
of piperine was 62 ppm in the model beverage containing the pepper
extract composite material.

Reference Comparative Example 5

[0125] Here, an extract of Piper longum of the Piperaceae family (content
of piperines: 300 to 1400 ppm, Maruzen Pharmaceuticals Co., Ltd.) was
used.

[0126] Into 99.43 parts by weight of water, 0.15 parts by weight of the
pepper extract, 0.3 parts by weight of citric acid, and 0.12 parts by
weight of trisodium citrate were dispersed, and the dispersion was
stirred with a mixer for 30 seconds. Thus, a pepper extract-containing
model beverage was prepared. The pepper extract-containing model beverage
was heated to 93° C., sterilized by being held at 90° C.
for 3 minutes, and then packed into a pouch. Thereafter, the pouch was
held in a constant-temperature water bath at 83° C. for 5 minutes
to perform a second sterilization. The amount of piperine was 0.25 ppm in
the prepared pepper extract-containing model beverage.

[0127] The model beverages prepared in Reference Example 5 and Reference
Comparative Example 5 were stored at 60° C. Piperine in the
samples before the storage, after one-week storage, and after two-week
storage was quantitatively determined by liquid chromatography. As the
ratio of remaining piperine, the values after one-week storage and two
week storage were represented by percentage, with a value of piperine
before the storage (0 weeks) being employed as 100%. FIG. 6 shows the
results. As is apparent from FIG. 6, the decomposition of the piperine
was more prevented in Reference Example 5 than in Reference Comparative
Example 5. From the results described above, it has been found that the
present invention makes it possible to prevent the decomposition of a
pepper extract in the presence of water, and to improve the stability
thereof.

Pretreatment Method for Liquid Chromatography

[0128] Regarding Reference Example 5, 10 g of the model beverage was
centrifuged (at 3000 rpm for 10 minutes), and then the supernatant was
removed. To the deposit, 3 ml of DMSO (dimethyl sulfoxide) was added, and
the mixture was ultrasonicated to dissolve the deposit. Moreover, the
mixture was diluted with methanol to 50 ml, filtered through a 0.45-μm
filter, and then used as a test liquid.

[0129] Regarding Reference Comparative Example 5, the sample was diluted
with methanol, then filtered through a 0.45-μm filter, and used as a
test liquid.

[0131] A deodorized fish oil "DHA-22HG" containing 22% or more of DHA
(manufactured by Maruha Nichiro Foods, inc.) was used as an unsaturated
fatty acid.

[0132] To 0.9 parts by weight of a phytosterol ester, 0.455 parts by
weight of the deodorized fish oil containing DHA was added. The mixture
was heated to 70° C. with string, and the deodorized fish oil was
dissolved therein. Thus, a phytosterol ester in which the deodorized fish
oil containing DHA was dissolved was prepared. Separately, 10 parts by
weight of γ-cyclodextrin and 5 parts by weight of water (90°
C.) were mixed with each other to prepare a mixture (paste). To the mixed
paste, the phytosterol ester in which the deodorized fish oil containing
DHA was dissolved was added. The mixture was kneaded for 10 minutes by
using a mortar, while being heating to 70° C. Thus, a composite
material was prepared. To the composite material, 82.895 parts by weight
of water was added with mixing. Subsequently, 0.5 parts by weight of
citric acid and 0.25 parts by weight of trisodium citrate were added
thereto and mixed therewith. Furthermore, the resultant mixture was
stirred with a homomixer at 5000 rpm for 2 minutes to obtain a
homogeneous white liquid. The white liquid was heated to 93° C.
with string, then packed into a colorless transparent glass container,
and then cooled. Thus, a packed beverage was produced. Note that the pH
of the beverage was 3.4.

Reference Comparative Example 6-1

[0133] A deodorized fish oil "DHA-22HG" containing 22% or more of DHA
(manufactured by Maruha Nichiro Foods, inc.) was used as an unsaturated
fatty acid.

[0134] To 0.9 parts by weight of a phytosterol ester, 0.455 parts by
weight of the deodorized fish oil containing DHA was added. The mixture
was heated to 70° C. with string, and the deodorized fish oil
containing DHA was dissolved therein. Thus, a phytosterol ester in which
the deodorized fish oil containing DHA was dissolved was prepared.
Separately, 0.5 parts by weight of an emulsifier was dissolved in 14.5
parts by weight of water (70° C.). To the emulsion, the
phytosterol ester in which the deodorized fish oil containing DHA was
dissolved was added, and the mixture was stirred with a homomixer at 5000
rpm for 10 minutes. Thus, an emulsion was prepared. To the emulsion,
82.895 parts by weight of water was added with mixing, and subsequently
0.5 parts by weight of citric acid and 0.25 parts by weight of trisodium
citrate were added thereto and mixed therewith. Then, the mixture was
heated up to 93° C. with string, packed into a colorless
transparent glass container, and then cooled. Thus, a packed beverage was
produced. Note that the pH of the beverage was 3.4.

Reference Comparative Example 6-2

[0135] A deodorized fish oil "DHA-22HG" containing 22% or more of DHA
(manufactured by Maruha Nichiro Foods, inc.) was used as an unsaturated
fatty acid.

[0136] To 0.9 parts by weight of refined rapeseed oil, 0.455 parts by
weight of the deodorized fish oil containing DHA was added. The mixture
was heated to 70° C. with string, and the deodorized fish oil
containing DHA was dissolved therein. Thus, refined rapeseed oil in which
the deodorized fish oil containing DHA was dissolved was prepared.
Separately, 0.5 parts by weight of an emulsifier was dissolved in 14.5
parts by weight of water (70° C.). To the emulsion, the refined
rapeseed oil in which the deodorized fish oil containing DHA was
dissolved was added, and the resultant mixture was stirred with a
homomixer at 5000 rpm for 10 minutes. Thus, an emulsion was prepared. To
the emulsion, 82.895 parts by weight of water was added with mixing, and
subsequently 0.5 parts by weight of citric acid and 0.25 parts by weight
of trisodium citrate were added thereto and mixed therewith. Thereafter,
the mixture was heated to 93° C. with string, then packed into a
colorless transparent glass container, and then cooled. Thus, a packed
beverage was produced. Note that the pH of the beverage was 3.4.

(Evaluation of Beverages)

[0137] The packed beverages were placed in a thermostatic chamber ("SANYO
GROWTH CABINET", temperature: 25° C., illuminance: 10000 lx), and
stored for 6 days. After the storage, the beverages were subjected to
sensory evaluation in terms of the odor (fishy odor). The blending ratios
and the results of the sensory evaluation are shown in the following
Table 10. From these results, it has been found that the present
invention makes it possible to prevent the deterioration of the
deodorized fish oil containing DHA.

[0138] A deodorized fish oil "DHA-22HG" containing 22% or more of DHA
(manufactured by Maruha Nichiro Foods, inc.) was used as an unsaturated
fatty acid.

[0139] To 0.9 parts by weight of a phytosterol ester, 0.455 parts by
weight of the deodorized fish oil containing DHA was added. The mixture
was heated to 70° C. with string, and the deodorized fish oil
containing DHA was dissolved therein. Thus, a phytosterol ester in which
the deodorized fish oil containing DHA was dissolved was prepared.
Separately, 10 parts by weight of γ-cyclodextrin and 5 parts by
weight of water (90° C.) were mixed with each other to prepare a
mixture (paste). To the mixed paste, the phytosterol ester in which the
deodorized fish oil containing DHA was dissolved was added. The mixture
was kneaded for 10 minutes by using a mortar, while being heated to
70° C. Thus, a composite material was prepared. To the composite
material, 82.895 parts by weight of water was added with mixing, and
subsequently 0.5 parts by weight of citric acid and 0.25 parts by weight
of trisodium citrate were added thereto and mixed therewith. Furthermore,
the resultant mixture was stirred with a homomixer at 5000 rpm for 2
minutes to obtain a homogeneous white liquid. The white liquid was heated
to 93° C. with string, then packed into a colorless transparent
glass container, and then cooled. Thus, a packed beverage was produced.
Note that the pH of the beverage was 3.4.

Reference Comparative Example 7

[0140] A deodorized fish oil "DHA-22HG" containing 22% or more of DHA
(manufactured by Maruha Nichiro Foods, inc.) was used as an unsaturated
fatty acid.

[0141] A mixture (paste) was prepared by mixing 10 parts by weight of
γ-cyclodextrin and 5 parts by weight of water (90° C.) with
each other. To the mixed paste, the deodorized fish oil containing DHA
was added. The mixture was kneaded for 10 minutes by using a mortar,
while being heated to 70° C. Thus, a composite material was
prepared. To the composite material, 83.795 parts by weight of water was
added with mixing, and subsequently 0.5 parts by weight of citric acid
and 0.25 parts by weight of trisodium citrate were added thereto and
mixed therewith. Furthermore, the resultant mixture was stirred with a
homomixer at 5000 rpm for 2 minutes to obtain a homogeneous white liquid.
The white liquid was heated up to 93° C. with string, then packed
into a colorless transparent glass container, and then cooled. Thus, a
packed beverage was produced. Note that the pH of the beverage was 3.4.

(Evaluation of Beverages)

[0142] The packed beverages were placed in a thermostatic chamber ("SANYO
GROWTH CABINET", temperature: 25° C., illuminance: 10000 lx), and
stored for 6 days. After the storage, the beverages were subjected to
sensory evaluation in terms of the odor (fishy odor). Furthermore, the
peroxide values thereof were measured (testing method: an acetic
acid-isooctane method). The blending ratios and the results of the
sensory evaluation are shown in the following Table 11. From these
results, it has been found that the present invention makes it possible
to prevent the deterioration of the deodorized fish oil containing DHA.

[0143] Hereinafter, Examples of Japanese Patent Application No.
2008-328263 are described as Reference Examples of the food or active
pharmaceutical ingredient (hydrophilic component) to which the present
invention can be applied.

Reference Example 8

[0144] To 6.19 parts by weight of a phytosterol ester melted by heating to
60° C., 0.06 parts by weight of a sucrose fatty acid ester was
added, and mixed therewith. The mixture was stirred with a homogenizer at
7000 rpm for 30 seconds to obtain a homogeneous dispersion. Next, 0.69
parts of caffeine was added to the phytosterol ester in which the sucrose
fatty acid ester was dispersed. Then, the mixture was again stirred with
a homogenizer at 7000 rpm for 1 minute to obtain a homogeneous
dispersion. Thus, a first mixture was prepared. Separately from the first
mixture, 55.83 parts by weight of γ-cyclodextrin and 37.23 parts by
weight of water (60° C.) were added to a mortar, and mixed with
each other by using a pestle. Thus, a second mixture was prepared as a
paste. The first mixture and the second mixture were kneaded in a mortar
for 10 minutes to thereby form a composite material. The blended amounts
(g) in Reference Example 8 are shown in the following Table 12.

Reference Comparative Example 8

[0145] To a mortar, 55.83 parts by weight of γ-cyclodextrin and
43.48 parts by weight of water (60° C.) were added, and were mixed
with each other by using a pestle. Thus, a mixture was prepared as a
paste. To the mixture, 0.69 parts by weight of caffeine was added, and
the resultant mixture was kneaded in hot water (60° C.) for 10
minutes. Thus, a composite material was formed. The blended amounts (g)
in Reference Comparative Example 8 are shown in the following Table 12.

[0146] At the ratios shown in the following Table 13, water was added to
and mixed with each of the composite materials obtained in Reference
Example 8 and Reference Comparative Example 8, and then sensory
evaluation was conducted. In addition, comparison was made with a mixture
of caffeine and water being employed as Reference Example.

[0147] The bitter taste was apparently more reduced in Reference Example 8
than in Reference Comparative Example 8 and Reference Example. The bitter
taste was more reduced in Reference Comparative Example 8 than in
Reference Example, but the bitter taste was still noticed in Reference
Comparative Example 8.

[0148] To 6.21 parts by weight of a phytosterol ester melted by heating to
60° C., 0.06 parts by weight of a sucrose fatty acid ester was
added, and mixed therewith. The mixture was stirred with a homogenizer at
7000 rpm for 30 seconds to obtain a homogeneous dispersion. Next, 0.62
parts by weight of vitamin B1 was added to the phytosterol ester in which
the sucrose fatty acid ester was dispersed. Then, the mixture was again
stirred with a homogenizer at 7000 rpm for 1 minute to obtain a
homogeneous dispersion. Thus, a first mixture was prepared. Separately
from the first mixture, 55.87 parts by weight of γ-cyclodextrin and
37.24 parts by weight of water (60° C.) were added to a mortar,
and mixed with each other by using a pestle. Thus, a second mixture was
prepared as a paste. The first mixture and the second mixture were
kneaded in a mortar for 10 minutes to thereby form a composite material.
The blended amounts (g) in Reference Example 9 are shown in the following
Table 14.

Reference Comparative Example 9

[0149] To a mortar, 55.87 parts by weight of γ-cyclodextrin and
43.51 parts by weight of water (60° C.) were added, and mixed with
each other by using a pestle. Thus, a mixture was prepared as a paste. To
the mixture, 0.62 parts by weight of vitamin B1 was added, and the
mixture was kneaded in a hot water (60° C.) for 10 minutes. Thus,
a composite material was formed. The blended amounts (g) in Reference
Comparative Example 9 are shown in the following Table 14.

[0150] At the ratios shown in the following Table 15, a 0.1% citric acid
solution was added to and mixed with each of the composite materials
obtained in Reference Example 9 and Reference Comparative Example 9, and
then sensory evaluation was conducted. In addition, a mixture obtained by
dissolving vitamin B1 in a 0.1% citric acid solution was employed as
Reference Example.

[0151] The bitter taste was apparently more reduced in Reference Example 9
than in Reference Comparative Example 9 and Reference Example. The bitter
taste was slightly reduced in Reference Comparative Example 9 as compared
with Reference Example, but the strong bitter taste was still noticed in
Comparative Example 9.

[0152] To 9.0 parts by weight of a phytosterol ester melted by heating to
60° C., 2.1 parts by weight of a glycerin fatty acid ester and 2.3
parts by weight of red beet pigment were added, and the mixture was
stirred with a homogenizer at 7000 rpm for 1 minute to obtain a
homogeneous dispersion. Thus, a first mixture was prepared. Separately
from the first mixture, 43.3 parts by weight of γ-cyclodextrin and
43.3 parts by weight of water (60° C.) were added to a mortar, and
mixed with each other by using a pestle. Thus, a second mixture was
prepared as a paste. The first mixture and the second mixture were
kneaded in a mortar for 10 minutes. Thus, a composite material having a
pink color tone was formed. The blended amounts (g) in Reference Example
10 are shown in the following Table 16.

Reference Comparative Example 10

[0153] To a mortar, 43.3 parts by weight of γ-cyclodextrin and 54.4
parts by weight of water (60° C.) were added, and mixed with each
other by using a pestle. Thus, a mixture was prepared as a paste. To this
mixture, 2.3 parts by weight of red beet pigment was added, and the
resultant mixture was kneaded in hot water (60° C.) for 10
minutes. Thus, a composite material having a pink color tone was formed.

[0154] The blended amounts (g) in Reference Comparative Example 10 are
shown in the following Table 16.

[0155] At the ratios shown in the following Table 17, water was added to
and mixed with each of the composite materials obtained in Reference
Example 10 and Reference Comparative Example 10, and then each composite
material in water was packed and sealed in a transparent pouch. In
addition, as Reference Example, red beet pigment and water were mixed
with each other at the ratio shown in Table 17, and were packed and
sealed in a transparent pouch. These pouches were stored in a
thermostatic chamber at 65° C. for 14 hours, and the change in
color tone before and after storage was visually evaluated.

[0156] The pink color tone of Reference Example 10 was kept even after the
storage. In contrast, the pink color tone of each of Reference
Comparative Example 10 and Reference Example was completely lost, and
these liquids had appearances which were transparent but slightly mixed
with an orange color.